Jonathan Grayer has spent his career in education.
As CEO of Kaplan, the 1982 Staples High School and ’86 Harvard University graduate turned the test prep company into the 2nd largest online education provider in the world.
He retired in 2008, then started Imagine Learning. He now serves as chair and CEO. Its digital curriculums make enormous differences in some of the largest and neediest public school districts in America.

Jonathan Grayer
Grayer is a philanthropist too. His main passions are cancer research and post-secondary schooling. His Kaplan Educational Foundation — “Rhodes Scholars for Community Colleges” — sends students from 2-year schools to Ivy League and other top universities.
But Grayer has not forgotten his Westport roots. And he knows that in this affluent community, plenty of families cannot afford the enormous (and skyrocketing) cost of college.
“It can be a lonely journey — especially with all the pressures already on kids,” he says.
So when he heard (via “06880”) that in conjunction with their 40th reunion, his Staples class was raising funds for Staples Tuition Grants, something clicked.
He sent a personal $25,000 check. Together with more than $5,000 in donations from reunion-goers, the result is an endowed fund, named for The Staples Class of 1982.
It’s believed to be the biggest class gift in STG’s 79-year history.

Staples Class of 1982 reunion organizers (from left) Dixie Webb O’Brien, Kim Hamer and Jeff Ruden enjoy the festivities.
Grayer did not make it back to Westport for the reunion. He was hosting a large family gathering at his Sagaponack home.
But his gift was noted often.
And it will be remembered for many years to come by Staples graduates who will benefit from a college education, thanks to the care and generosity of alumni who preceded them more than 40 years earlier.
(To learn more about Staples Tuition Grants — including how to donate — click here.)
(Like Staples Tuition Grants, “06880” is a non-profit. Please click here to support this blog.)